1,2-Dibromoethane → HCID 22104147, compound

HRID 1939612Notes

Reaction equation

HRID 1939612 reaction equation
[OH-].[K+].Cl.[NH2:4]O.[CH2:6]([S:13][C:14]1[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:24](=[O:27])([O-])[O-].[K+].[K+].BrCCBr>CO>[CH2:6]([S:13][C:14]1[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=1[C:16]1[O:18][CH2:19][CH2:24][O:27][N:4]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 5

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 775668Benzoic acid, 2-[(phenylmethyl)thio]-, methyl ester

Product 1

HCID 22104147HCID 22104147, compoundYield 21.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
40 °C

Procedure

160 g (2.86 mol) of potassium hydroxide in 700 ml of methanol are added dropwise, at room temperature, to a mixture of 98.7 g (1.42 mol) of hydroxylamine hydrochloride and 700 ml of methanol. Subsequently, 184 g (0.712 mol) of methyl 2-(benzylthio)benzoate are added in portions at room temperature. The mixture is stirred at 40° C. overnight. 98.1 g (0.712 mol) of potassium carbonate are then added, 601 g (3.20 mol) of 1,2-dibromoethane are added dropwise, and the mixture is left stirring at 60° C. overnight. Subsequently, the solvent is distilled off under reduced pressure. The residue is partitioned between methylene chloride and water. The organic phase is dried and the solvent is distilled off under reduced pressure. The residue is stirred up with absolute ethyl alcohol. The solid is filtered off with suction and dried under high vacuum. 43.1 g (21% of theory) of 1-benzylthio-2-(5,6-dihydro-[1,4,2]-dioxazin-3-yl)benzene are obtained as a pale yellow solid. Melting point: 73°-77° C.

Workup

  1. waitthe mixture is left
  2. stirringstirring at 60° C. overnight
  3. distillationSubsequently, the solvent is distilled off under reduced pressure
  4. customThe residue is partitioned between methylene chloride and water
  5. customThe organic phase is dried
  6. distillationthe solvent is distilled off under reduced pressure
  7. stirringThe residue is stirred up with absolute ethyl alcohol
  8. filtrationThe solid is filtered off with suction
  9. customdried under high vacuum

Sources & evidence

ORD record
ord-100118ea4d22424ebc442eb03511fc14
Source dataset
uspto-grants-1997_12
Patent number
US05696257

Reaction notes

Loading…